Abstract
For reasons of economy and pollution, solvent-free methods are of great interest in order to modernize classical procedures making them more clean, safe and easy to perform. Reactions on solid mineral supports, reactions without any solvent/support or catalyst, and solid-liquid phase transfer catalysis can be thus employed with noticeable increases in reactivity and selectivity. A comprehensive review of these techniques is presented here. These methodologies can moreover be improved to take advantage of microwave activation as a beneficial alternative to conventional heating under safe and efficient conditions with large enhancements in yields and savings in time.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Keinan E, Mazur Y (1977) J. Am Chem Soc 99:3861
Laszlo P (1987) In: Preparative chemistry using supported reagents. Academic Press, London
Smith K (1992) In: Solid support and catalysts in organic synthesis. Ellis Horwood PTR Prentice Hall, Chichester
Kabalka GW, Pagni RM (1997) Tetrahedron 53:7999
Toda F (1993) Synlett 304
Toda F (1995) Acc Chem Res 28:480
Starks CM (1971) J Am Chem Soc 93:195
Bram. G, Loupy A, Sansoulet J (1985) Israel J Chem 26:291
Bram G, Galons H, Labidalle S, Loupy A, Miocque M, Petit A, Pigeon P, Sansoulet J ( 1989) Bull Soc Chim Fr 247
Foucaud A, Bram G, Loupy A (1993) In: Preparative chemistry using supported reagents, Academic Press, London, chap 17, p 317
Hondrogiannis G, Than CL, Pagni RM, Kabalka GW, Herold S, Ross E, Green J, Mc Ginnis M (1994) Tetrahedron Lett 35:6211
Bram G, D’Incan E, Loupy A ( 1982) New J Chem 573, 689
Loupy A, Seyden-Penne J (1980) Tetrahedron 36:1937
Pagni RM, Kabalka GW, Boothe R, Gaetano K, Stewart LJ, Conaway R, Dial C, Gray D, Larson S, Luidhardt T (1988) J Org Chem 53:4477
Kropp PJ, Daus KA, Tubergen MW, Kepler KD, Wilson VP, Craig SL, Baillargeon MM, Breton GW (1993) J Am Chem Soc 115:3071
Czech B, Quici S, Regen SL (1980) Synthesis 113
Tan CL, Pagni RM, Kabalka GW, Hillmyer M, Woosley J (1992) Tetrahedron Lett 33:7709
Bodwell GJ, Hougton TJ, Koury HE, Yarlagadda B (1995) Synlett 751
Parks GA (1965) Chem Rev 65:177
Varma RS, Varma M (1992) Tetrahedron Lett 33:5937
Texier-Boullet F (1985) Synthesis 679
Rosini G, Ballini R, Sorrenti P (1983) Tetrahedron 39:4127
Ranu BC, Bhars S (1992) Tetrahedron 48:1327
Loupy A, Tchoubar B (1992) In: Salt effects in organic and organometallic chemistry, VCH, Weinheim, p 37
Clark JH (1980) Chem Rev 80:429
Yamawaki J, Ando T (1979) Chem Lett 755
Villemin D, Ricard M (1984) Tetrahedron Lett 39:1059
Oussaïd A, Loupy A unpublished results; Oussaïd A ( 1997) PhD thesis, Orsay, Paris-South University
Ando T, Kawate T, Ichihara J, Hanafusa T (1984) Chem Lett 725
Anufriev VP, Norikov V (1995) Tetrahedron Lett 36:2515; Ando T, Kawate T, Ichihara J, Hanafusa T (1983) Bull Soc Chim Jpn 56:1885
Ando T, Sumi S, Kawate T, Ichihara J, Hanafusa T ( 1984) J Chem Soc Chem Commun 439
Posner GH, Rogers DZ (1977) J Am Chem Soc 99:8208,8214
Ranu B, Majee A, Das AR (1995) Synth Commun 25:263
Dhavale DD, Sindkhedkar MD, Mali RS (1995) J Chem Res S 414
Pagni RM, Kabalka GW, Hondrogiannis G, Bains S, Anosike P, Kurt R (1993) Tetrahedron 49:6743
Bains S, Pagni RM, Kabalka GW, Palla C ( 1994) Tetrahedron: Asymmetry 5:2263
Kamitori Y, Hojo M, Masuda R, Yoshida T ( 1985) Tetrahedron Lett 26:4767
Kodomari M, Sakamoto T, Yoshitomi S (1990) J Chem Soc Chem Commun 701
Ranu BC, Ghosh K, Jana U (1996) J Org Chem 61:9546
Breton GW, Kurtz MJ, Kurtz SL (1997) Tetrahedron Lett 38:3825
Farwaha R, de Mayo P, Schauble JH, Toong YC (1985) J Org Chem 50:149
Slayton RM, Franklin NR, Tro NJ (1996) J Phys Chem 100:15551
Santaniello E (1993) In: Preparative chemistry using supported reagents. Academic Press, London, chap 18, p 345
Ranu BC, Sarkar A, Saha M, Chakraborty R (1994) Tetrahedron 50:6579; Ranu BC, Majee A, Sarkar A (1998) J Org Chem 63:370
Clark JH, Cork DG (1983) J Chem Soc Perkin Trans 1 2253
Bram G, Loupy A (1993) In: Preparative chemistry using supported reagents. Academic Press, London, chap 20, p 387
Kotushi H, Shimanouchi T, Oshima R, Fujiwara S (1998) Tetrahedron 54:2709
Veselovsky VV, Gybin AS, Lozanova AV, Moiseenkov AM, Smit WA, Caple R (1988) Tetrahedron Lett 29:175
Patil VJ, Mävers U ( 1996) Tetrahedron Lett 37:1281
Bram G, D’Incan E, Loupy A (1981) J Chem Soc Chem Commun 1066
Barry J, Bram G, Decodts G, Loupy A, Pigeon P, Sansoulet J (1983) Tetrahedron 39: 2669
Bram J, Loupy A, Roux-Schmitt MC, Sansoulet J, Strzalko T, Seyden-Penne J (1987) Synthesis 56
Huang B, Gupton JT, Hansen KC, Idoux JP (1996) Synth Commun 26:165
Balogh M, Laszlo P (1993) In: Organic chemistry using clays, reactivity and structure concepts in organic chemistry, vol 29. Springer, Berlin Heidelberg New York
Izumi K, Urabe K, Onaka M (1992) In: Zeolite, clay and heteropoly acids in organic reactions, VCH, Weinhein, chap 1, p 21
Toshima K, Ishizuka T, Matsuo G, Nakata M (1995) Synlett 306
Toshima K, Miyamoto N, Matsuo G, Nakata M, Matsumura S (1996) J Chem Soc Chem Commun 1379
Toshima K, Ushiki Y, Matsuo G, Matsumara S ( 1997) Tetrahedron Lett 38:7375
Kellendonk FJA, Heinerman JJL, Van Santen RA (1987) In: Preparative chemistry using supported reagents. Academic Press, London, chap 23, p 455
Theng BKG (1979) In: Formation and properties of clay-polymer complexes, Elsevier, Amsterdam
Diddams P (1992) In: Solid supports and catalysts in organic synthesis, Ellis Horwood PTR Prentice Hall, Chichester, chap 1, p 23
Ben alloum A, Labiad B, Villemin D (1989) J Chem Soc Chem Commun 386
Pério B, Dozias MJ, Jacquault P, Hamelin J (1997) Tetrahedron Lett 38:7867
Devic M, Schirmann JP, Decarreau A, Bram G, Loupy A, Petit A (1991 ) New J Chem 15:949
Bram G, Loupy A, Majdoub M, Petit A (1991) Chem Ind (London) 396
Cornélis A, Dony C, Laszlo P, Nsunda KM (1991) Tetrahedron Lett 32:1423; Clark JH, Kybett AP, Mac Quarrie DJ, Barlow SJ, Landon P (1989) J Chem Soc Chem Commun 1353
Cornélis A, Gestermans A, Laszlo P, Mathy A, Zieba I (1990) CatalLett 6:103
Bram G, Loupy A, Villemin D (1992) In: Solid supports and catalysts in organic synthesis, Ellis Horwood PTR Prentice Hall, Chichester, chap 12, p 301
Corey EJ, Seebach D (1966) J Org Chem 31:4097
Loupy A, Sansoulet J, Harris AR (1989) Synth Commun 19:2939
Harris AR (1988) Synth Commun 18:659
Toda F, Yagi M, Kiyoshige K (1988) J Chem Soc Chem Commun 958
Toda F, Tanaka K, Hamai K (1990) J Chem Soc Perkin Trans 1 3207
Kammoun N, Le Bigot Y, Delmas M, Boutevin B (1997) Synth Commun 27:2777
Im J, Kim S, Hahn B, Toda F ( 1997) Tetrahedron Lett 38:451
Toda F, Aakai H ( 1990) J Org Chem 55:3446
Rajagopal D, Rajagopalan K, Swaminathan S (1996) Tetrahedron: Asymmetry 7:2189
Keller P (1987) Macromolecules 20:462; Majdoub M (1998) PhD thesis, University Tunis II
Strzelecka H, Jallabert C, Veber M, Malthête J (1988) Mol Cryst Liq Cryst 136:347; Bayle JP, Bui E, Perez F, Courtieu J (1989) Bull Soc Chim Fr 532
Loupy A, Sansoulet J, Vaziri-Zand F (1987) Bull Soc Chim Fr 1027
Barry J, Bram G, Decodts G, Loupy A, Orange C, Petit A, Sansoulet J (1985) Synthesis 40
Loupy A, Sansoulet J, Pedoussaut M (1986) J Org Chem 51:740
Le Ngoc T, Duong-Lieu H, Nguyen-Ba H, Radhakrishna AS, Singh BB, Loupy A (1993) Synth Commun 23:1379
Diez-Barra E, De la Hoz A, Diaz-Ortiz A, Prieto P (1992) Synlett 893
Diez-Barra E, De la Hoz A, Diaz-Ortiz A, Prieto P (1993) Synth Commun 23:1935
Diaz-Ortiz A, Prieto P, Loupy A, Abenhaïm D ( 1996) Tetrahedron Lett 37:1936
Loupy A, Luche JL (1997) In: Handbook of phase transfer catalysis, Chapman and Hall, London, chap 11, p 369
Sasson Y, Weiss M, Loupy A, Bram G, Pardo C (1986) J Chem Soc Chem Commun 1250
Loupy A, Pardo C (1988) Synth Commun 18:1275
Loupy A, Bram G, Sansoulet J, Vaziri-Zand F (1986) New J Chem 10:765
Oussaid A, Pentek E, Loupy A (1997) New J Chem 21:1339
Kornblum N, Seltzer R, Haberfield P ( 1963) J Am Chem Soc 85:1148
Matsumoto K (1980) Angew Chem 82:1046
Bram G, Sansoulet J, Galons H, Miocque M (1988) Synth Commun 18:367
Mirza-Aghayan M, Etemad-Moghadam G, Zaparucha A, Berlan J, Loupy A, Koenig M (1995) Tetrahedron: Asymmetry 6:2643
Loupy A, Sansoulet J, Zaparucha A, Mérienne C (1989) Tetrahedron Lett 30:333
Loupy A, Zaparucha A (1993) Tetrahedron Lett 34:473
Jones GB, Chapman BJ (1995) Synthesis 475
Conn RSE, Lovell AV, Karady S, Weinstock LM (1986) J Org Chem 51:4710
Diez-Barra E, De la Hoz A, Merino S, Sanchez-Verdu P (1997) Tetrahedron Lett 38: 2359
Diez-Barra E, De la Hoz A, Merino S, Sanchez-Verdu P (1997) In: Halpern ME (ed) Phase transfer catalysis, mechanism and syntheses. ACS Symposium Series 659, chap 14, p 181
Diez-Barra E, De la Hoz A, Merino S, Sanchez-Verdu P, Rodriguez A ( 1998) Tetrahedron 54:1835
Van Eldick R, Hubbard CD (1997) In: Chemistry under extreme or non-classical conditions, Wiley, New York
Loupy A (1993) Spectra Analyse 175:33
Abramovitch RA (1991) Org Prep Proc Int 23:685; Caddick S (1995) Tetrahedron 51:10403
Jullien SC, Delmotte M, Loupy A, Jullien H (1991) In: Microwaves and high frequencies, International Congress, Nice (France) 8–10 October, p 654
Stuerga D, Gaillard P ( 1996) Tetrahedron 52:5505
Lewis DA, Summers JD, Ward TC, Mc Grath JE (1992) J Polym Sci A 30:1647
Binner JGP,H assine NA, Cross TE (1995) J Mater Sci 30:5389
Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L,R ousell J ( 1986) Tetrahedron Lett 27:279
Giguere RJ, Bray TL, Duncan SM, Majetich G (1986) Tetrahedron Lett 27:4945
Loupy A, Petit A, Hamelin J, Texier-Boullet F, Jacquault P, Mathé D ( 1998) Synthesis, 1213
Villemin D, Thibault-Starzyk F (1991) J Chem Educ 346
Jacquault P (1992) EU Patent 545995 AI Prolabo Co
Guttierez E, Loupy A, Bram G, Ruiz-Hitzky E (1989) Tetrahedron Lett 30:945
Trehan IR, Brar JS, Arora AK, Kad GL ( 1997) J Chem Educ 74:324
Singh J, Kaur J, Nayyar S, Kad GL ( 1998) J Chem Res S 280
Perez ER, Marrerro AL, Perez R, Autié MA (1995) Tetrahedron Lett 36:1779
Acosta A, De la Cruz P, De Miguel P, Diez-Barra A, De la Hoz A, Langa F, Loupy A, Majdoub M, Martin N, Sanchez C, Seoane C (1995) Tetrahedron Lett 36:2165
Csiba M, Cléophax J, Loupy A, Malthête J, Gero S ( 1993) Tetrahedron Lett 34:1787
Bram G, Loupy A, Majdoub M, Gutierrez E, Ruiz-Hitzky E ( 1990) Tetrahedron 46:5167
Van den Eynde JJ, Fromont D ( 1997) Bull Soc Chim Belg 106:393
Ranu BC, Saha M, Bhar S (1997) Synth Commun 27:621
Michaud D, Texier-Boullet F, Hamelin J (1997) Tetrahedron Lett 38:7563
Varma VS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:4603
Varma VS, Lamture JB, Varma M (1993) Tetrahedron Lett 34:3029
Varma VS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:3207
Oussaid A, Loupy A (1997) J Chem Res S 342
Benhaliliba H, Derchour A, Bazureau JP, Texier-Boullet F, Hamelin J (1998) Tetrahedron Lett 39:541
Suarez M, Loupy A, Perez E, Moran T, Gerona G, Morales A, Autié M (1996) Heterocyclic Commun 2:275
Cotterill IC, Usyatinsky AY, Arnold JM, Clark DS, Dordick JS, Michels PC, Khmelnitsky YL (1998) Tetrahedron Lett 39:1117
Villemin D, Ben Alloum A (1990) Synth Commun 20:3325
Villemin D, Ben Alloum A, Thibault-Starzyk (1992) Synth Commun 22:1359
Bougrin K, Soufiaoui M, Loupy A, Jacquault P ( 1995) New J Chem 19:213
Limousin C, Cléophax J, Petit A, Loupy A, Lukacs G (1997) J Carbohydr Res 16:327
Abenhaïm D, Loupy A, Mahieu C, Séméria D ( 1994) ) Synth Commun 24:1809
Jiang Y, Wang Y, Deng R, Mi A (1997) In: Halpern ME (ed) Phase transfer catalysis,mechanisms and syntheses. ACS Symposium Series 659, chap 16, p 203
Loupy A, Pigeon P, Ramdani M (1996) Tetrahedron 52:6705
Loupy A, Petit A, Ramdani M, Yvanaeff C, Majdoub M, Labiad B, Villemin D (1993) Can J Chem 71:90
Abenhaïm D, Loupy A, Ngoc Son CP, Nguyen Ba H ( 1994) Synth Commun 24:1199
Loupy A, Pigeon P, Ramdani M, Jacquault P ( 1994) Synth Commun 24:159
Lewis DA (1992) Mat Res Soc Symp Proc 269:21
Barnier JP, Loupy A, Pigeon P, Ramdani M, Jacquault P (1993) J Chem Soc Perkin Trans 1 397
Bogdal D, Pielichowski J, Boron A (1996) Synlett 873
Bogdal D, Pielichowski J, Jaskot K (1997) Heterocycles 45:715
Oussaid A, Le Ngoc T, Loupy A (1997) Tetrahedron Lett 38:2451
Diez-Barra E, Abenhaïm D, De la Hoz A, Loupy A, Sanchez-Migallon A (1994) Heterocycles 38:793
Jaisinghani HG, Khadilkar BM (1997) Tetrahedron Lett 39:6875
Borah HN, Boruah RC, Sandhu JS (1998) J Chem Res S 272
Loupy A, Petit A, Bonnet-Delpon D (1995) J Fluorine Chem 75:215
Boruah B, Prajapati D, Boruah A, Sandhu JS (1997) Synth Commun 27:2563
Diez-Barra E, De la Hoz A, Carrillo-Munoz JR, Diaz-Ortiz A, Gomez-Escalonilla MJ, Moreno A, Langa F (1996) Tetrahedron 52:9237
Bortolussi M, Bloch R, Loupy A (1998) J Chem Res S 34
Guibé-Jampel E, Rousseau G (1987) Tetrahedron Lett 28:3563
Carrillo-Munoz JR, Bouvet D, Guibé-Jampel E, Loupy A, Petit A (1996) J Org Chem 61:7746
Chemat F, Poux M, Berlan J ( 1994) J Chem Soc Perkin Trans 2 2597
Porcelli M, Cacciapuoti G, Fusco S, Massa R, d’Ambrosio G, Bertoldo C, De Rosa M, Zappia V (1997) FEBS Lett 402:102
Gelo-Pujic M, Guibé-Jampel E, Loupy A, Galema SA, Mathé D ( 1996) J Chem Soc Perkin Trans 1 2777
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1999 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Loupy, A. (1999). Solvent-free Reactions. In: Knochel, P. (eds) Modern Solvents in Organic Synthesis. Topics in Current Chemistry, vol 206. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-48664-X_7
Download citation
DOI: https://doi.org/10.1007/3-540-48664-X_7
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-66213-6
Online ISBN: 978-3-540-48664-0
eBook Packages: Springer Book Archive